EPEREZOLID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H23FN4O5
Molecular Weight	394.3974
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC=C(N3CCN(CC3)C(=O)CO)C(F)=C2

InChI

InChIKey=SIMWTRCFFSTNMG-AWEZNQCLSA-N

InChI=1S/C18H23FN4O5/c1-12(25)20-9-14-10-23(18(27)28-14)13-2-3-16(15(19)8-13)21-4-6-22(7-5-21)17(26)11-24/h2-3,8,14,24H,4-7,9-11H2,1H3,(H,20,25)/t14-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9333036
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8834904

Eperezolid is an antibiotic agent developed for the treatment of a wide range of bacterial infections. The drug exerts its action by binding to 50 S ribosome subunit causing the inhibition of protein synthesis in bacterias. Eperezolid was tested in preclinical in vivo models of different becterial diseases in which it was shown to be active.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9333036	Binding Agent 1064		20.0 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10582874	Curative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections.	1996 Feb 2	8576909
Oxazolidinones: a review.	2000 Jan	10718097
Oxazolidinone antibacterial agents: a critical review.	2003	12678835
Simple method for the assay of linezolid in Brain Heart Infusion broth by high-performance liquid chromatography.	2004 Jan	14872541
Synthesis and antibacterial activity of dihydro-1,2-oxazine and 2-pyrazoline oxazolidinones: novel analogs of linezolid.	2005 Jun 2	15911264
Synthesis and SAR of novel oxazolidinones: discovery of ranbezolid.	2005 Oct 1	16054358
Synthesis and antibacterial activities of eperezolid analogs with glycinyl substitutions.	2009 Jul	19544480
Production of icaADBC-encoded polysaccharide intercellular adhesin and therapeutic failure in pediatric patients with Staphylococcal device-related infections.	2010 Mar 15	20230642
Pharmacokinetics of Linezolid and Ertapenem in experimental parapneumonic pleural effusion.	2010 May 18	20482752

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Eperezolide was active against all classes of pneumococci, with MIC90s of 0.5 ug/ml.

Name

Type

Language

EPEREZOLID

Official Name

English

Eperezolid [WHO-DD]

Common Name

English

U-100,592

Code

English

U-100592

Code

English

eperezolid [INN]

Common Name

English

ACETAMIDE, N-((3-(3-FLUORO-4-(4-(HYDROXYACETYL)-1-PIPERAZINYL)PHENYL)-2-OXO-5-OXAZOLIDINYL)METHYL)-, (S)-

Common Name

English

EPEREZOLID [USAN]

Common Name

English

N-[[(S)-3-[3-fluoro-4-(4-glycoloyl-1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258